T&C Travel Guide: The Best of Martha's Vineyard

Tourism on Martha's Vineyard—just "the Vineyard" to locals—began in the 1800s, when the island became a summer "camp" destination for Methodists from around the country who'd come for annual meetings, with a side of seafood and sea bathing. And while the island just eight miles off the coast of Cape Cod has since become a preferred getaway for presidents (from Kennedy to Obama) and celebrities (Jake Gyllenhaal and Chelsea Handler, for example), the quaintness has never really subsided—even as mainstream brands creep their way into town. (SoulCycle, for instance, has a pop-up kicking off July 3rd.)

Those who prefer it to Nantucket (and you're either a Vineyarder or a Nantucketer) say it's more laidback, less polished, a place where well-to-do New England meets town greens, lobster, and the men who fish for them.

Here are a few insider highlights.

Where to Stay

Summercamp

The exterior of the Summercamp.

Courtesy of Lark Hotels

The former Wesley Hotel's recent makeover pays homage to Oak Bluffs's history with rustic touches like wall-mounted vintage tennis rackets, retro snacks in the Camp Canteen, and movie night in the rec hall, but there are plenty of modern draws, including bright décor and harbor views. The 95-room, family-friendly hotel is a walk from the ferry as well as the town beach, the carousel, and Oak Bluffs's vast range of excellent restaurants, from the ultra-casual Offshore Ale Co. to the more refined Sweet Life Café. Whichever you choose, save room for ice cream at Ben & Bill's, home of the semi-world famous lobster ice cream, far tastier than it sounds.BOOK NOW70 Lake Avenue, Oak Bluffs, 508-693-6611

Winnetu

The exterior of the beachfront favorite, Winnetu.

Courtesy of Winnetu

The longstanding beachfront favorite excels in convenience—a removed location on South Beach but steps away from the heart of busy Edgartown with plenty of family-friendly offerings, including evening s'mores and rides on the hotel's antique fire truck, as well as a life-sized chess board, tennis, yoga, and bikes to borrow. Recently renovated accommodations come in all sizes and configurations, from one- to four-bedroom hotel suites to three- to five-bedroom private cottages.BOOK NOW31 Dunes Road, Edgartown, 508-310-1733

Lambert's Cove Inn, Farm and Restaurant

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With 15 rooms spread across seven acres of gardens and a short walk to Lambert's Cove beach, the inn—universally regarded as the island's most romantic place to stay—offers easy access to activity, but plenty of corners to curl up with a book. You may find yourself reluctant to leave the grounds: With a newly expanded produce garden and the additions of 50 hens and two goats, Ava and Zsa Zsa, to provide fresh eggs and cheese, farm-to-table here is as authentic as it gets.BOOK NOW90 Manaquayak Road, Vineyard Haven

Where to Eat

20byNine

The island's first craft beer and whiskey bar.

Adam Jaime Photography

The island's first craft beer and whiskey bar (motto: "Do not fear the whiskey") classes up Oak Bluffs with an extensive list of American-made malts and blends and a sustainable, local menu to down them with (all food items come with suggested drink pairings). Go for brunch, where the chicken and waffles or baby burgers with glazed bacon settle in excellently with the off-menu Bloody Mary.20bynine.com, 16 Kennebec Avenue, Oak Bluffs, 508-338-2065

Newes from America Pub

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If you want a classic Vineyard vibe—and some truly life-changing fish and chips—the Newes, at the base of Edgartown's historic Kelley House, won't disappoint. Limited release New England craft beers and live music find a home against the backdrop of a 1742-era building with exposed wooden beams and, best of all, plenty of local characters.kelley-house.com, 23 Kelly St, Edgartown, 508-627-7900

Since its 2012 opening, the Port Hunter—named after a British steamship that collided with ocean tug Covington off the coast of Massachusetts in 1918—has been one of Edgartown's hottest tables, with nautical decor and a seasonal menu. Summertime highlights include Buffalo brussels sprouts with blue cheese mousse, bluefish cakes, and fish tacos made with Vineyard flounder. Often-lengthy waits (it's that good) are made more bearable with a SRO raw bar, shuffleboard, and live music most nights. In 2016, the Port Hunter owners debuted The Covington across the street, where the slightly more formal fare, and scene, includes ceviche of Menemsha sea bass, duck from Good Farm in Vineyard Haven, and pasta with ragu of island-grown pork.theporthunter.com, 55 Main Street, Edgartown, 508-627-7747, and 52 Main Street, Edgartown, 508-627-7678

Back Door Donuts

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At night, the unassuming Martha's Vineyard Gourmet Café & Bakery opens its back doors to donut fans willing to weave through an hour-long line in a back-alley lot for still-warm donuts—in a variety of flavors, but plain is best—and apple fritters. Lines start at 7 a.m. and linger till 1 p.m. Get there on the early side to avoid the rowdier sugar fiends.mvbakery.com, 5 Post Office Square, Oak Bluffs, 508-693-3688

Where to Shop

Alley's General Store

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The classic country store, and the island's oldest operating business, has been known for more than a century as a "dealer in almost everything." And they mean it: Satisfy your bread and coffee needs; buy stamps; and stock up on all the classic beach town essentials, like towels, toys, bug spray, and penny candy. In season, visit the farm stand out back for apples, eggs, pies—you name it, they've got it.mvpreservation.corg, 1041 State Road, West Tisbury, 508-693-0088

Bunch of Grapes Bookstore

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The indie bookstore earned renown as an Obama family favorite, but it's been an island treasure for more than half a century, with particularly extensive children's book and cookbook selections, as well as all the of-the-moment beach reads.bunchofgrapes.com

The Allen Farm Sheep and Wool Company

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The historic family farm deals in friendly sheep, and visitor takeaways that include everything from grass-fed meat and eggs and gourmet items like olive oil, jams, and locally made sea salt mixes to knitwear, throws, and skeins of wool.allenfarm.com, 421 South Road, Chilmark, 508-645-9064

What to Do

Hit the Beach

Gay Head Cliffs

Getty Images

Obviously! You really can't go wrong with any Vineyard beach (unless you expect Caribbean water temps; this is the northeast, after all). But certainly, each one has its own personality. South Beach, in the Katama section of Edgartown, is an easy all-ages choice, with a wide, sandy beach and lifeguards on duty (in season). Families also love Edgartown's Norton Point, the best parts of which are accessible only by 4x4, where a small bay opposite the roaring ocean suits children (don't forget your oversand permit, or to deflate your tires). Lucy Vincent beach in Chilmark, a reported favorite of Jake Gyllenhaal, is for residents only (it's well worth the effort to befriend one). For those who like to work up a pre-swim sweat, the 1.5-mile trail through Great Rock Bight preserve in Chilmark can end with a splash in Vineyard Sound, while the private stretch of Squibnocket Beach (also in Chilmark) is a surfer's favorite. Gay Head in Aquinnah, on the westernmost part of the island, is one of the most picturesque, and romantic Vineyard islands, framed by looming clay cliffs with plenty of sandy nooks to camp out in.

Rent a Jeep

Renting a car makes for a fun and easy way to see the island.

Getty Images

It's not essential to have a car on-island—you'll find plenty to do within most towns, and taxis are easy enough to come by—but with so much acreage to explore, you'll be glad you did. Spring for a Jeep. You'll be glad you did that, too.

First pick up a cup of chowder and some stuffies at Larsen's Fish Market, maybe a bottle of wine from Vintage MV in Edgartown or a six-pack of local craft beer from Jim's Package Store in Oak Bluffs, then walk to Menemsha Public Beach in Chilmark. Get there by 6 p.m. for the best sunset on the island, and possibly the entire east coast.

Get some culture at Martha's Vineyard Playhouse

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The non-profit professional theater, built in 1833, hosts Monday evening "special performances" of new dramatic works by playwrights both local and non on its Patricia Neal stage, named after one of the playhouse's best patrons. There are also classic movie nights, live music, and a Poetry Café run by island poet laureate Arnie Reitman.mvplayhouse.org, 24 Church Street, Vineyard Haven, 508-696-6300

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